I have Bitbucket server and Jira installed on the same machine, I am using the same email server configuration for both tools, Jira works without any problem but in bitbucket, I am getting send fail with the following exception.
javax.mail.MessagingException: Could not convert socket to TLS
Email server configuration,
Use SSL/TLS if available checked
username and from address are the same
welcome to the Atlassian Community!
The error message suggests the secured (SSL/TLS) connection to the Office 365 mailserver could not be established, most likely due to some SSL certificate issues.
In case it was not just a temporary issue with Microsoft Cloud services I'd check on a lower level first if connection works (for example using a tutorial to be found on the internet). You said you have both services running on the same machine - therefore the check should show up no problems.
The next step I would take is to check if bitbucket is utilizing the appropriate SSL certificate for Microsoft 365 service. Probably Microsoft had to renew a SSL certificate on their end.
As a last resort a clean restart of Bitbucket might also help.
Please also check if there are further errors in log file that could be of help.
Hey Community! We’re willing to wager that quite a few of you not only use Bitbucket, but administer it too. Our team is excited to share that we’ll be releasing improvements throughout this month of...
Connect with like-minded Atlassian users at free events near you!Find an event
Connect with like-minded Atlassian users at free events near you!
Unfortunately there are no Community Events near you at the moment.Host an event
You're one step closer to meeting fellow Atlassian users at your local event. Learn more about Community Events